Water → (2,6-Dimethyl-4-phenylpyridin-3-yl)methanol

HRID 1182701Notes

Reaction equation

HRID 1182701 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[N:18]=[C:17]([CH3:19])[CH:16]=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]=1[C:10](OCC)=[O:11].O.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[CH3:7][C:8]1[C:9]([CH2:10][OH:11])=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[C:17]([CH3:19])[N:18]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 11414168Ethyl 2,6-dimethyl-4-phenylpyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 67434062(2,6-Dimethyl-4-phenylpyridin-3-yl)methanolYield 102.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

LiAlH4 (1 M solution in THF, 8.93 mL, 8.93 mmol) was added dropwise to a solution of ethyl 2,6-dimethyl-4-phenylnicotinate (940 mg, 3.57 mmol) in THF (38 mL) at 0° C. After stirring for 45 min, the reaction mixture was allowed to warm to room temperature and the stirring was continued for 75 min Water (0.2 mL) was added at 0° C. followed by NaOH (2 M, 0.2 mL) and water (0.2 mL). After the addition of excess EtOAc and filtration, the solvent was removed in vacuo providing (2,6-dimethyl-4-phenylpyridin-3-yl)methanol as a pale yellow gum (780 mg, >99%). ESI-MS [M+H]+=214.1.

Workup

  1. waitthe stirring was continued for 75 min
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e10665af230f4277a6bb6fcd00f55533
Source dataset
uspto-grants-2014_03
Patent number
US08664214B2

Reaction notes

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